When I was an undergrad I had a boyfriend who was from an extremely money family.

Back then and still to a huge extent I am kind of ... way of too big for my britches? Or at least my standard state of mind is friendly unimpressed? Like: "Oh you are super good at this thing, cool I do not care much let us hang out".

Friendly+too dumb to know I'm being cocky. Or maybe just that I don't intimidate easily or at all.

This has served me maybe too well as a strategy?

I just let him buy me shit whenever he felt like it and take me on vacations. I didn't move in with him though, we spent time at each other's places instead. We ended up breaking up after a couple of years and one of the reasons:

The only time I would be weird about the wealth disparity was when we were with his family and I would make an effort to appear so good a guy they wouldn't imagine I was a gold digger, like I wanted to seem like I was too good for their son/brother and maybe also by the transitive property too good for them.

I know it sounds super shitty and it was. I am not proud of it. I mean it worked also but not in a cool way.

It was a big part of why we broke up. His family didn't see through it but my ex did obviously. He did not like the way I was with them or what it implied about my feelings for him ... etc.

He just wanted me to be a normal lovable dirtbag. That is what he wanted in a guy. And it turned out I wasn't that.

Conversely: I was a mathematics major and he did something technical as well. I was a lot more gifted wrt to math than him and he was no slouch. When he hung out with my friends or studied for exams with us he was never too proud to ask for help and he never tried to seem more skilled than he was, he dealt with that stuff in like the best most secure way.

So ... yeah. Does that help?

I guess what I want to say is that if someone has more power than you, you shouldn't really act differently around them than you would if they didn't have that power. Probably. Ok so he doesn't think you have enough money to be with him. Doesn't that disqualify him as someone you want to be with anyway then? That is my feeling anyway.